71591-96-3

Basic information

• Product Name: (3E)-3-[(phenylamino)methylidene]-3,4-dihydro-2H-1-benzopyran-2,4-dione
• CAS NO: 71591-96-3
• Molecular Weight: 265.268
• Mol File: 71591-96-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (3E)-3-[(phenylamino)methylidene]-3,4-dihydro-2H-1-benzopyran-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3E)-3-[(phenylamino)methylidene]-3,4-dihydro-2H-1-benzopyran-2,4-dione(71591-96-3)
• EPA Substance Registry System: (3E)-3-[(phenylamino)methylidene]-3,4-dihydro-2H-1-benzopyran-2,4-dione(71591-96-3)

Safety Data

• Hazardous Substances Data: 71591-96-3(Hazardous Substances Data)

Upstream product

• 39079-62-4 chromone-3-carboxylic acid 
• 62-53-3 aniline 
• 51751-34-9 4-hydroxycoumarin-3-carboxaldehyde 
• 113326-75-3 N-((4-oxo-4H-chromen-3-yl)methylene)aniline oxide 

Downstream Products

• 100185-93-1 N,N''-Bis-<3-<(2,4-dioxochroman-3-yliden-methyl)-amino>-propyl>-N',N'''-bis-<5-(2-methacryloyloxy-ethoxycarbonyl-amino)-2-methyl-phenyl>-N,N''-ethandiyl-diharnstoff 
• 100185-91-9 N,N-Bis-<3-<(2,4-dioxochroman-3-yliden-methyl)amino>-propyl>-N'-<5-(2-methacryloyloxy-ethoxycarbonylamino)-2-methyl-phenyl>-harnstoff 
• 100200-24-6 N,N''-Bis-<3-<(2,4-dioxochroman-3-yliden-methyl)-amino>-propyl>-N',N'''-di-p-tolyl-N,N''-ethandiyl-diharnstoff 
• 100185-92-0 N,N''-Bis-<3-<(2,4-dioxochroman-3-ylidenmethyl)-amino>-propyl>-N',N'''-diphenyl-N,N''-ethandiyl-diharnstoff 
• 100185-90-8 N,N-Bis-<<(2,4-dioxochroman-3-yliden)-methylen>-3-aminopropyl>-N'-(4-tolyl)-harnstoff 

Relevant articles and documents

Synthesis and evaluation of chromone derivatives as inhibitors of monoamine oxidase

Abstract: Based on reports that chromone compounds are good potency inhibitors of monoamine oxidase (MAO), the present study evaluates the effect of substitution with flexible side chains on the 3 position on MAO inhibition potency. Fifteen chromone derivatives were synthesised by reacting aromatic and aliphatic amines and alcohols with chromone 3-carboxylic acid in the presence of carbonyldiimidazole (CDI). This yielded chromane-2,4-dione and ester chromone derivatives. Generally, the esters exhibited weak MAO inhibition, while the chromane-2,4-dione derivatives showed promise as selective MAO-B inhibitors with IC50 values in the micromolar range. Compound 14b, 3-[(benzylamino)methylidene]-3,4-dihydro-2H-1-benzopyran-2,4-dione, was the most potent MAO-B inhibitor with an IC50 value of 638?μM. This compound was shown to be a reversible and competitive MAO-B inhibitor with a Ki of 94?μM. In conclusion, the effect of chain elongation and introduction of flexible substituents on position 3 of chromone were explored and the results showed that aminomethylidene substitution is preferable over ester substitution. Good potency MAO-B inhibitors may act as leads for the design and development of therapy for Parkinson’s disease where these agents reduce the central metabolism of dopamine. Graphical abstract: [Figure not available: see fulltext.].

Thermal rearrangements of C-(4-Oxo-4H[1]benzopyran-3-yl)-N- phenylnitrone-a route to novel quinolino[2,3-b] chroman-12-ones

C-(4-Oxo-4H[1]benzopyran-3-yl)-N-phenylnitrones (1a-c) undergo facile rearrangements on refluxing in benzene, yielding 2-(N-phenylamino)-4-oxo- 4H[1]-benzopyran-3-carboxaldehydes (2a-c,70%) and 3-(phenyliminomethylene)- chroman-2,4-diones (3a-c, 25%). 2a-